The paper discusses the essence and features of telecommuting, communication costs and the problems of implementing compliance procedures to reduce the costs and risks. The paper’s aim is to analyze the risks with the introduction of telecommuting procedures in Russian and foreign companies in the period of lockdown caused by the new coronavirus infection COVID-19. Today, the COVID-19 pandemic continues to have a negative impact and create a critical situation in all spheres and industries, which causing destabilization of the economy and the labor market. One of the main recommendations of the World Health Organization is a physical distancing, limits of movements freedom, closure of some companies that are not vital, etc. Judging the above, the employer has to learn not only to carry out his activities, but also to survive in these conditions. This is the reason that many companies have to switch into the remote work process fully or partially as a temporary or alternative way of organizing work. The paper focuses on the directions and complexity of the tools choice for building connections between a workforce and management. Also, it analyzes the use of compliance to regulate communication relations, control communications and manage risks that arise from violations of the legislation, the regulations of regulators, the rules of self-regulatory organizations and internal documents. The authors compare a conception of compliance control, goals, processes, stages and effects of the use of the regulatory mechanism in the pandemic. Also, the authors give the respondents’ answers regarding the importance of compliance control, digital competencies for the high-quality performance of functions and communication at telecommuting. The results led to the conclusion that freelancing is not only a powerful incentive for changing employee’s behavior in conditions of uncertainty but also it brings an additional risk for all companies. Various digital monitoring tools aim to reflect the balance between security and personal freedom in the society infrastructure.